Iodoethane → HCID 13769233, compound

HRID 2232554Notes

Reaction equation

HRID 2232554 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].C([Li])CCC.[C:13]1([C:19]2[CH:28]=[C:27]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(I)C>CCCCCC.O1CCCC1.O.C(O)(=O)C.C(O)C.CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([CH:31]([CH2:30][CH2:29][C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:28]=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2]

Participants

11

Reactant 4

HCID 6340IodoethaneHCID 7912DiisopropylamineHCID 21283568HCID 21283568, compoundHCID 178418339Butyllithium

Product 1

HCID 13769233HCID 13769233, compound

Reagents, catalysts & solvents 6

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-70 °C

Procedure

Diisopropylamine (2.96 cc) is added to dry tetrahydrofuran (30 cc) placed under an atmosphere of nitrogen. The solution is stirred and cooled to -70° C. A 1.6M solution (11.3 cc) of butyllithium in hexane is then introduced in the course of 15 minutes, and then, after stabilization of the temperature at -70° C., a solution of ethyl 2-phenyl-4-quinolinebutanoate (3.8 g) in tetrahydrofuran (30 cc) is introduced in the course of 5 minutes. The mixture is stirred for 30 minutes at -70° C. and ethyl iodide (1.15 cc) and hexamethylphosphoramide (0.8 cc) in tetrahydrofuran (20 cc) are introduced in the course of 5 minutes. The mixture is stirred for 7 hours at -70° C. Ethanol (7 cc) is added followed by acetic acid (2 cc). The temperature is allowed to rise to room temperature (approximately 20° C.), and the reaction medium is diluted with water (300 cc) and extracted with ethyl ether (2×100 cc). The ether phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue is chromatographed on silica gel using a cyclohexane/ethyl acetate (90:10 by volume) mixture. Ethyl α-ethyl-2-phenyl-4-quinolinebutanoate (1.8 g), m.p. 76° C., is thereby isolated.

Workup

  1. stirringThe mixture is stirred for 30 minutes at -70° C.
  2. stirringThe mixture is stirred for 7 hours at -70° C
  3. customto rise to room temperature
  4. custom(approximately 20° C.)
  5. extractionextracted with ethyl ether (2×100 cc)
  6. washThe ether phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel using a cyclohexane/ethyl acetate (90:10 by volume) mixture

Sources & evidence

ORD record
ord-162c4b8a2b6e4e35937d28d16dc0f5ad
Source dataset
uspto-grants-1988_11
Patent number
US04788204

Reaction notes

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